GB1107968A - Process for the trimerization of butadiene - Google Patents

Process for the trimerization of butadiene

Info

Publication number
GB1107968A
GB1107968A GB28866/66A GB2886666A GB1107968A GB 1107968 A GB1107968 A GB 1107968A GB 28866/66 A GB28866/66 A GB 28866/66A GB 2886666 A GB2886666 A GB 2886666A GB 1107968 A GB1107968 A GB 1107968A
Authority
GB
United Kingdom
Prior art keywords
butadiene
cyclododecatriene
trimerization
sesquichloride
catalyst
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB28866/66A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1107968A publication Critical patent/GB1107968A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
    • C07C2/44—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion of conjugated dienes only
    • C07C2/46—Catalytic processes
    • C07C2/465—Catalytic processes with hydrides or organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/135—Compounds comprising a halogen and titanum, zirconium, hafnium, germanium, tin or lead
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cyclododecatriene-(1,5,9) is prepared in yields of 85-95% by contacting butadiene with a catalyst formed by reacting (a) an organo-aluminium compound Z25.- 3.5.Al2Cl3.5- 2.5 where Z is C2-C4 alkyl, or phenyl, (b) 0.3-0.9 moles water per mole (a), and (c) a titanium compound T : A4 wherein A is at least one of Cl, Br, I or OR, R being C1-C20, the molar ratio (a) to (c) being from 3:1 to 30:1, and carrying out the trimerization at 20-120 DEG C. The catalyst is preferably prepared in situ, and one component may be introduced as a gas with the butadiene feed. The preferred aluminium sesquichloride is ethylaluminium sesquichloride. Reaction may be effected in an inert solvent such as benzene, cyclohexane, hexane or, particularly, cyclododecatriene product, and the water may be dissolved therein or added as vapour in an inert gas carrier e.g. N2 or in the butadiene feed. The pressure is not critical and may be 0.5-50 atmos. It is stated that isoprene may be similarly trimerized.
GB28866/66A 1965-06-29 1966-06-28 Process for the trimerization of butadiene Expired GB1107968A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US46810465A 1965-06-29 1965-06-29
US551889A US3381045A (en) 1965-06-29 1966-05-23 Cyclododecatriene 1, 5, 9 process

Publications (1)

Publication Number Publication Date
GB1107968A true GB1107968A (en) 1968-03-27

Family

ID=27042284

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28866/66A Expired GB1107968A (en) 1965-06-29 1966-06-28 Process for the trimerization of butadiene

Country Status (5)

Country Link
US (1) US3381045A (en)
BE (1) BE683285A (en)
DE (1) DE1593245A1 (en)
GB (1) GB1107968A (en)
NL (1) NL151053B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4877789A (en) * 1971-12-27 1973-10-19

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3546309A (en) * 1969-05-29 1970-12-08 Du Pont Trimerization of butadiene
US3523980A (en) * 1969-06-10 1970-08-11 Du Pont Trimerization of butadiene
JPS494215B1 (en) * 1970-06-18 1974-01-31
ES2197041T3 (en) 1999-07-13 2004-01-01 Degussa Ag PROCEDURE FOR THE MANUFACTURE OF CATALYZER FEEDBACK CYCLING.
DE102006022014A1 (en) * 2006-05-10 2007-11-15 Degussa Gmbh Process for the preparation of cyclododecatriene

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1086226B (en) * 1959-03-10 1960-08-04 Studiengesellschaft Kohle Mbh Process for the preparation of cyclododecatriene (1, 5, 9)
US3076045A (en) * 1959-03-10 1963-01-29 Studiengesellschaft Kohle Mbh Process for the production of cyclododecatri-(1, 5, 9)-enes
GB987423A (en) * 1961-06-30 1965-03-31 Basf Ag Production of oligomers of 1,3-dienes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4877789A (en) * 1971-12-27 1973-10-19
JPS5710551B2 (en) * 1971-12-27 1982-02-26

Also Published As

Publication number Publication date
NL6609061A (en) 1966-12-30
DE1593245A1 (en) 1971-10-07
BE683285A (en) 1966-12-28
US3381045A (en) 1968-04-30
NL151053B (en) 1976-10-15

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